A snow-covered town with a river running through it, surrounded by mountains and trees.

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Check availability on Winchester Hotels with Pool

Our top choices for Winchester hotels with a pool

Indoor pool

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Splash into comfort at this indoor pool oasis offering year-round aquatic escape in Keene.
The price is ฿4,520
฿4,905 total
includes taxes & fees
16 Jul - 17 Jul
Keene Elm City Hotel, an Ascend Collection Hotel
Indoor pool

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,014 reviews)
  • cleanliness
    Dive into a serene indoor pool retreat with hot tub and sauna, perfect for year-round relaxation near Wachusett Mountain.
The price is ฿5,122
฿5,721 total
includes taxes & fees
19 Jul - 20 Jul
The Colonial Hotel
Indoor pool, pool loungers

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (833 reviews)
  • cleanliness
    Relaxing indoor pool retreat with comfortable loungers sets the perfect stage for your Vermont ski getaway.
The price is ฿4,430
฿4,873 total
includes taxes & fees
27 Jul - 28 Jul
Comfort Inn & Suites Brattleboro I-91
Indoor pool

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (1,000 reviews)
  • cleanliness
    Immerse in rejuvenating waters at this mountain-adjacent hotel featuring a pristine indoor pool and relaxing hot tub sanctuary.
The price is ฿4,366
฿4,802 total
includes taxes & fees
22 Jul - 23 Jul
Hampton Inn Brattleboro
Indoor pool

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (392 reviews)
  • cleanliness
    Splash into serenity at this inviting indoor pool hotel, where year-round swimming meets complete comfort and relaxation.
The price is ฿5,327
฿5,780 total
includes taxes & fees
29 Jul - 30 Jul
Hampton Inn & Suites Keene
Indoor pool

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
9.0 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Splash into family fun with a year-round indoor pool perfect for kids at this rural Vermont retreat.
The price is ฿4,219
฿4,641 total
includes taxes & fees
26 Jul - 27 Jul
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Indoor pool, open 6:00 AM to 10:00 PM, pool loungers

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,000 reviews)
  • cleanliness
    Splash into luxury at this hotel's sparkling indoor pool, complete with plush sun loungers and serene atmosphere.
The price is ฿4,989
฿5,413 total
includes taxes & fees
16 Jul - 17 Jul
Best Western Plus Keene Hotel
Seasonal outdoor pool

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (497 reviews)
  • cleanliness
    Refreshing poolside retreat in Black Mountain with seasonal swimming and scenic garden views.
The price is ฿4,855
฿5,341 total
includes taxes & fees
19 Jul - 20 Jul
Black Mountain Inn
Indoor pool

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.6 out of 10, Excellent, (1,006 reviews)
  • cleanliness
    Dive into the year-round aquatic escape at this art deco hotel with a pristine indoor pool.
The price is ฿6,012
฿6,523 total
includes taxes & fees
5 Aug - 6 Aug
Courtyard by Marriott Keene Downtown
Exterior

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (58 reviews)
  • cleanliness
    Tranquil outdoor pool retreat complements this historic bed & breakfast with garden views and mountain adventures.
The price is ฿9,869
฿10,857 total
includes taxes & fees
16 Jul - 17 Jul
Inn on Putney Road
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at hotels with a pool in Winchester

Breakfast included
4 stars

Top Winchester Hotel Reviews

Colonial Motel

Colonial Motel

8/10 Good
"Room wa very spacious, didn't care for the carpeting. Beds was great. Refrigerator and microwave was convenient."
George 1-night trip
Posted 11 hours ago
Colonial Motel

Frequently asked questions

What are some accommodation options with pools in Winchester?
The Colonial Hotel: Features a sauna, an indoor pool and free self parking. Keene Elm City Hotel, an Ascend Collection Hotel: Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access. Best Western Plus Keene Hotel: Features buffet, an indoor pool and free self parking. Latchis Hotel: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Colonial Motel: Provides buffet, an indoor pool and free self parking.
What is there to see and do in Winchester?
Make a point to visit attractions such as Cass Pond and Rhododendron State Park. During your stay, visit sights such as Winchester Speedpark, New England Sweetwater Farm & Distillery and Conant Public Library. Take in the natural beauty of Winchester with the lakeside setting.
When is the best time to book a hotel with a pool in Winchester?
Taking the local weather in Winchester into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winchester are January, March, February and November, with each month seeing an average of 26 cm of snowfall.